Month: July 2021

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 3972-56-3, name is 1-tert-Butyl-4-chlorobenzene, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 3972-56-3

General procedure: Arylchloride (1 mmol, 1 equiv), decane (internal standard, 0.2 mL), and anhydrous Et2O (5 mL) were sequentially added to a pre-dried Schlenk flask equipped with a magnetic stirrer and a rubber septum under argon. The flask was cooled to ?95°C (methanol/liquid nitrogen bath) followed by the dropwise addition of a previously prepared LiDBB solution (ca. 0.25 M in THF, 2 mmol, 8 mL, 2 equiv). After addition and stirring for 5 min at this temperature, aryllithium reagent 2 was obtained. The corresponding arylzinc reagent 5 was prepared by the addition of ZnCl2 solution (1.0 M in THF, 1 mmol, 1 mL) followed by warming to r.t. The yield of the aryllithium or arylzinc reagent was determined by GC analysis of an aliquot of the resulting arylzinc reagent quenched with asolution of iodine in anhydrous THF in the presence of an internal standard (decane).

According to the analysis of related databases, 3972-56-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Shen, Zhi-Liang; Sommer, Korbinian; Knochel, Paul; Synthesis; vol. 47; 17; (2015); p. 2617 – 2630;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 3970-51-2, name is 5-Chloro-1H-indene, A new synthetic method of this compound is introduced below., COA of Formula: C9H7Cl

Intermediate 8: 1,1-dimethylethyl 5-chloro-1’H-spiro[indene-1,4′-piperidine]-1′-carboxylate. 5-chloro-lH-indene (2 g, 13 mmol) dissolved in dry THF (10 mL) was added to a stirring solution of IM lithium hexamethyldisilazide (LHMDS) (28 mL, 28 mmol) at 0 C. The mixture was stirred for 1 hr, and 1,1 -dimethylethyl bis(2- chloroethyl)carbamate (3.2 g, 13 mmol) dissolved in THF (10 mL) was added dropwise. The resulting purple solution was taken out of the ice bath and allowed to stir overnight at room temperature. The mixture was diluted with water and DCM, and the layers were separated. The organic layer was dried over sodium sulfate, evaporated, then purified by flash column chromatography to yield 2 grams of a 50:50 mix of 5-Cl and 6-Cl regiomers. The regioisomers were separated by HPLC. Analysis by HMBC showed that the peak eluting second was the desired 5-Cl regioisomer. MS (ES) m/e 320 [M+H]+. 1H NMR (400 MHz, CDCl3, delta): 7.30 (d, J = 1.76 Hz, IH), 7.22 (d, , J = 8.03 Hz, IH), 7.17 (dd, J = 1.76 Hz, 8.03 Hz, IH), 6.91 (d, J = 5.64 Hz, IH), 6.73 (d, J = 5.64 Hz, IH), 4.19 (m, 2H), 3.12 (m, 2H), 1.98 (m, 2H), 1.52 (s, 9H), 1.32 (m, 2H).

The synthetic route of 3970-51-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2009/23754; (2009); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 1207625-18-0,Some common heterocyclic compound, 1207625-18-0, name is 3-Chloro-7H-pyrrolo[2,3-c]pyridazine, molecular formula is C6H4ClN3, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

ie f-Butyl 4-[4-(7/-/-pyrrolo[2,3-c]pyridazin-3-yl)-1 /-/-pyrazol-1 -yl]piperidine-1-carboxylateTo a well stirred suspension of 3-chloro-7/-/-pyrrolo[2,3-c]pyridazine (136 mg, 0.89 mmol), 4-[4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)pyrazol-1-yl]-piperidine-1-carboxylic acid ie f-butyl ester (367 mg, 0.97 mmol, 1.1 eq), and cesium carbonate (526 mg, 1.62 mmol, 1.8 eq) in 20% aqueous dioxane (20 mL) was bubbled nitrogen for 15 min at room temperature. To the resulting mixture was added Pd(PPh3)4 (51 mg, 0.045 mmol), then the mixture was heated at 100 C for 16 h. The reaction mixture was cooled to RT and concentrated under reduced pressure. The residue was partitioned between water and DCM (30 mL each), and the aqueous layer was extracted with more methylene chloride (2×15 mL). The combined organic layers were washed with water (20 mL) followed by brine (10 mL), dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with 5 to 10% methanol in methylene chloride as eluent to yield the title compounds as off-white solid. 1H NMR (300 MHz, CDCI3): delta = 1.45 (s, 9H), 1 .81-2.35 (m, 4H), 2.78-3.05 (m, 4H), 4.12 (mc, 1 H), 6.62 (d, J = 3.3 Hz, 1 H), 7.62 (d, J = 3.3 Hz, 1 H), 7.93 (s, 1 H), 8.08 (s, 1 H), 8.20 (s, 1 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Chloro-7H-pyrrolo[2,3-c]pyridazine, its application will become more common.

Reference:
Patent; OSI PHARMACEUTICALS, LLC; LI, An-Hu; MULVIHILL, Mark, J.; STEINIG, Arno, G.; WO2011/143646; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 39226-95-4, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 39226-95-4 as follows.

Example 4 Synthesis of N-(2,3-dichlorobenzyl)-4,5-dihydro-1H-imidazol-2-amine A mixture of 5.32 g of (2,3-dichlorophenyl)methanamine 10 and 4.56 g of 4,5-hihydro-1H-imidazole-2-sulfonic acid are mixed in 40.0 mL ethanol (EtOH) and heated in a sealed tube at 90 C. for 16 hours. Then, the reaction mixture was cooled to room temperature. Next, the ethanol was removed under vacuum. The remaining residue was basified with aqueous sodium bicarbonate solution and the pH was adjusted to about 10 with 2M sodium hydroxide. The aqueous layer was extracted three times with 400 mL of chloroform/isopropanol (3:1). The pooled organic layer was dried over magnesium sulfate and the mixture was then filtered. The filtrate was added to amino-modified silica gel (4-5% methanol in dichloromethane) and afforded 3.99 g of Compound 11 as a yellow solid.1H NMR (300 MHz, CD3OD): delta 7.43 (dd, J=7.8, 1.8 Hz, 1H, 7.37-7.33 m, 1H), 7.26 (t, J=7.8 Hz, 1H), 4.43 (s, 2H), 3.51 (s, 4H)

According to the analysis of related databases, 39226-95-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ALLERGAN, INC.; US2009/306161; (2009); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 102-49-8,Some common heterocyclic compound, 102-49-8, name is 3,4-Dichlorobenzylamine, molecular formula is C7H7Cl2N, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a solution of the compound 2 (0.15 g, 0.39 mmol) in CH2Cl2 (10 mL) were added 3,4-dichlorobenzylamine (0.22 g, 0.47 mmol), HATU (0.178 g, 0.468 mmol), DIPEA (79 muL, 0.975 mmol). The mixture was stirred at room temperature for 45 min. Subsequently, the reaction mixture was transferred to a separators funnel and washed with 1 N HCl (10 mL), saturated NaHCO3, water, and brine. The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure to obtain compound 3a (0.177 g, 97percent yield) as a yellow oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3,4-Dichlorobenzylamine, its application will become more common.

Reference:
Article; Wang, Boyu; Wang, Kuanglei; Meng, Peipei; Hu, Yaping; Yang, Fei; Liu, Kemin; Lei, Zaiqiang; Chen, Binfeng; Tian, Yongshou; Bioorganic and Medicinal Chemistry Letters; vol. 28; 21; (2018); p. 3477 – 3482;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 918538-05-3, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 918538-05-3 name is 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

In a 25mL reaction vial, Pd(PPh3)2Cl2 (19mg, 0.027mmol) and 2N Na2CO3 solution (0.27mL, 0.54mmol) were added to a solution of 1-methyl-1H-pyrazole-4-boronic acid pinacol ester (55mg, 0.27mmol) and 12 (50mg, 0.27mmol) in dioxane (5mL). The mixture was stirred at 70C for 16h under N2 atmosphere. The reaction mixture was cooled to room temperature and filtrated. The filtrate was diluted with H2O (100mL) and then extracted with EtOAc, and the organic layer was dried over anhydrous Na2SO4, After filtration, the filtrate was evaporated and purified by chromatography (petroleum ether/EtOAc, 5:1) to give the product 20 as a yellow solid (55mg, 88%). MS (ESI) m/z: [M+H]+=234. 1H NMR (400M, DMSO-d6) delta 8.87 (s, 1H, ArH), 8.38 (s, 1H, ArH), 8.14 (s, 1H, ArH), 7.53 (d, 1H, J=4.8Hz, ArH), 7.10 (dd, 1H, J1=2.4Hz, J2=4.8Hz, ArH), 3.98 (s, 3H, ArCH3) ppm.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine, and friends who are interested can also refer to it.

Reference:
Article; Xin, Minhang; Zhang, Liandi; Tang, Feng; Tu, Chongxing; Wen, Jun; Zhao, Xinge; Liu, Zhaoyu; Cheng, Lingfei; Shen, Han; Bioorganic and Medicinal Chemistry; vol. 22; 4; (2014); p. 1429 – 1440;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 6775-78-6, name is 6-Chloroimidazo[1,2-b]pyridazine, belongs to chlorides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 6775-78-6, COA of Formula: C6H4ClN3

478 mg (3.1 1 mmol) of 6-chloroimidazo[1 ,2-b]pyridazine were introduced into 10 mL of chloroform under argon and, while cooling in ice, 664 mg (3.73 mmol) of N- bromo-succinimide were added. After the addition was complete, the reaction mixture was stirred at room temperature overnight. The reaction mixture was then mixed with water and ethyl acetate and, after addition of saturated sodium bicarbonate solution, the phases were separated. The aqueous phase was extracted three more times with ethyl acetate. The combined organic phases were then washed with saturated sodium chloride solution and dried over sodium sulfate. In the final removal of the solvent in vacuo, the desired product was isolated in quantitative yield in the form of an amorphous white solid which was employed without further chromatographic purification in subsequent reactions.1H-NMR (CHLOROFORM-d): delta [ppm] = 7.12 (d, 1 H); 7.79 (s, 1 H); 7.90, (d, 1 H).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 6-Chloroimidazo[1,2-b]pyridazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; SCHULZE, Volker; EIS, Knut; PUEHLER, Florian; ZORN, Ludwig; SUeLZLE, Detlev; LIENAU, Philip; WENGNER, Antje Margret; PETERSEN, Kirstin; BOeMER, Ulf; WO2015/104254; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 33406-96-1, name is 1-Chloro-4-fluoro-2-methylbenzene, This compound has unique chemical properties. The synthetic route is as follows., Formula: C7H6ClF

2-Chloro-5-fluoro-4-nitrotoluene. To a stirred solution of 2-chloro-5-fluorotoluene (10.356 g, 71.628 mmol, Lancaster, used as received) in conc. H2 SO4 (70 mL) at 0 C., KNO3 (7.252 g, 71.72 mmol) was added in four equal portions. The resulting pale yellow solution was allowed to warm to room temperature and was stirred overnight at room temperature. It was then poured into ice water (350 g) and extracted with ether (3*100 mL). Ether was dried over anhydrous Na2 SO4, removed under vacuum, and the resulting oil was dried further under vacuum to afford 12.277 g (90%) of the title compound as an oil, which was used as such for the next reaction; 1 H NMR (CDCl3); delta2.459 (s, 2H), 7.193 (d, 1H, J1 =11.1 Hz), 8.083 (d, 1H, J1 =6.6 Hz).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 33406-96-1.

Reference:
Patent; State of Oregon, acting by and through the Oregon State Board of Higher Education, acting for and on behalf of the Oregon Health Sciences University and the University of Oregon, Eugene Oregon; Acea Pharmaceuticals, Inc.; The Regents of the University of California; US5631373; (1997); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 13918-92-8, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 13918-92-8, name is 2,4-Difluorobenzene-1-sulfonyl chloride, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a solution of 8 (0.2 mmol, 1 equiv) in THF (1 mL) was added the sulfonyl chloride, sulfamoyl chloride or acid chloride (0.24 mmol, 1.2equiv), followed by TEA (0.30 mmol, 1.5 equiv). The mixture was stirred at rt for 3 h. Water (0.4 mL), EtOAc (3 mL) and then saturated NaHCO3 solution (0.8 mL) were added. After 10 min, the aqueous layer was removed. Celite (600 mg) was added to the organic layer and the solvent was evaporated. Flash chromatography using silica gel with an EtOAc/hexanes gradient provided the purified sulfonamide, sulfamide or amide.

The chemical industry reduces the impact on the environment during synthesis 2,4-Difluorobenzene-1-sulfonyl chloride. I believe this compound will play a more active role in future production and life.

Reference:
Article; Amato, George; Wiethe, Robert; Manke, Amruta; Vasukuttan, Vineetha; Snyder, Rodney; Runyon, Scott; Maitra, Rangan; Bioorganic and Medicinal Chemistry; vol. 27; 16; (2019); p. 3632 – 3649;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 14752-66-0, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 14752-66-0 name is Sodium 4-chlorobenzenesulfinate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

A mixture of THF, K2CO3 (0.77 g 0 006 mol) and sodium 4-chloro- benzenesulfinate(0.75 g, 3.7 mmol) was stirred for 15 en blanket and cooled to 0-5 C. Naphth-2-ylmethylbromide (0.81 g, 3.7 mmol) was added to the reaction mixture. The mixture was stirred at 65 – 67 C for two hours and the solvent was removed by distillation. The resultant solid residue was recrystallized from isopropanol to give the title product, 0.30g, 51% yield, 99% purity by HPLC

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Sodium 4-chlorobenzenesulfinate, and friends who are interested can also refer to it.

Reference:
Patent; WYETH; RAVEENDRANATH, Sanjay; RAVEENDRANATH, Vijay; RAVEENDRANATH, Girija; WO2008/157216; (2008); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics